ContaminantDB: Quassin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 01:46:19 UTC

Update Date

2016-11-09 01:19:02 UTC

Accession Number

CHEM030256

Identification

Common Name

Quassin

Class

Small Molecule

Description

Bitter constituent of Quassia amara (Surinam quassia) and Picrasma excelsa (Jamaican quassiawood) Quassin is a white bitter, crystalline substance extracted from the quassia tree. It is the bitterest substance found in nature with a bitter threshold of 0.08ppm and it is 50 times more bitter than quinine.

Contaminant Sources

FooDB Chemicals
STOFF IDENT Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Nigakilactone D	HMDB
Quassin	MeSH

Chemical Formula

C₂₂H₂₈O₆

Average Molecular Mass

388.454 g/mol

Monoisotopic Mass

388.189 g/mol

CAS Registry Number

76-78-8

IUPAC Name

4,15-dimethoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-4,14-diene-3,11,16-trione

Traditional Name

quassin

SMILES

COC1=CC(C)C2CC3OC(=O)CC4C(C)=C(OC)C(=O)C(C34C)C2(C)C1=O

InChI Identifier

InChI=1S/C22H28O6/c1-10-7-14(26-5)20(25)22(4)12(10)8-15-21(3)13(9-16(23)28-15)11(2)18(27-6)17(24)19(21)22/h7,10,12-13,15,19H,8-9H2,1-6H3

InChI Key

IOSXSVZRTUWBHC-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Quassinoids

Alternative Parents

Substituents

C-20 quassinoid skeleton
Quassinoid
Naphthopyran
Naphthalene
Delta valerolactone
Cyclohexenone
Delta_valerolactone
Pyran
Oxane
Carboxylic acid ester
Ketone
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.043 g/L	ALOGPS
logP	2.73	ALOGPS
logP	2.24	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	18.08	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	104.2 m³·mol⁻¹	ChemAxon
Polarizability	41 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0odj-0209000000-e284c8786161fb2c0379	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-7e540d032cd53e8bed92	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0072-0019000000-17bae020877053ca3160	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9453000000-d49be7bcb435b4da0085	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-9ac13bf543d17c7a8ccd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000l-0009000000-ac85f55d6c57b2e68200	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002f-3019000000-c8ca587aaf4c7a602155	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000l-0009000000-7da52e89cb542bda89c4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dr-0029000000-a48b2bc4a57e0ce12130	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00n0-3897000000-6f3942b0306db2d2d125	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-7f16ac45973a6479b3e5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0009000000-f8847d5c1dba461f6dac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0avr-0029000000-d98d24d4098095349f75	Spectrum